The biosynthesis of indolocarbazoles in a heterologous E. coli host

ChemBioChem

Volumn 4, Issue 1, 2003, Pages 114-117

  Hyun, Chang Gu ^a   Bililign, Tsion ^a,b   Liao, Jianchun ^a   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b Weill Cornell Graduate School of Biomedical Sciences   (United States)

Author keywords

Biosynthesis; Gene locus; Heterologous expression; Natural products; Rebeccamycin

Indexed keywords

CARBAZOLE DERIVATIVE; INDOLOCARBAZOLE; K 252A; PROTEIN KINASE C INHIBITOR; REBECCAMYCIN; STAUROSPORINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BIOSYNTHESIS; DRUG SYNTHESIS; ESCHERICHIA COLI; GENE LOCUS; HETEROLOGOUS EXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOST; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; CARBAZOLES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA, BACTERIAL; DRUG EVALUATION, PRECLINICAL; ESCHERICHIA COLI; GENE LIBRARY; INDOLES; MASS SPECTROMETRY;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; LECHEVALIERIA AEROCOLONIGENES; SACCHAROTHRIX;

EID: 0037415016     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200390004     Document Type: Article

References (34)

1. a) S. Omura, Y. Sasaki, Y. Iwai, H. Takeshima, J. Antibiot. 1995, 48, 535;
2. b) G. W. Gribble, S. J. Berthel in Studies in Natural Products Chemistry, Vol. 12, Elsevier Science, Amsterdam, 1993, p. 365.
3. a) H. Kase, K. Iwahashi, Y. Matsuda, J. Antibiot. 1986, 39, 1059;
4. b) S. Nakanishi, Y. Matsuda, K. Iwahashi, H. Kase, J. Antibiot. 1986, 39, 1066;
5. c) T. Yasuzawa, T. Iida, M. Yoshida, N. Hirayama, M. Takahashi, K. Shirahata, H. Sano, J. Antibiot. 1986, 39, 1072;
6. d) T. Tamaoki, H. Nomoto, I. Takahashi, Y. Kato, M. Morimoto, F. Tomita, Biochem. Biophys. Res. Commun. 1986, 135, 397.
7. a) D. E. Nettleton, T. W. Doyle, B. Krishnan, G. K. Matsumoto, J. Clardy, Tetrahedron Lett. 1985, 26, 4011;
8. b) J. A. Bush, B. H. Long, J. J. Catino, W. T. Bradner, K. Tomita, J. Antibiot. 1987, 40, 668.
9. a) C. Bailly, X. Qu, D. E. Graves, M. Prudhomme, J. B. Chaires, Chem. Biol. 1999, 6, 277.
10. a) M. J. Slater, R. Baxter, R. W. Bonser, S. Cockerill, K. Gohil, N. Parry, J. E. Robinson, R. Randall, C. Yeates, W. Snowden, A. Walters, Bioorg. Med. Chem. Lett. 2001, 11, 1993;
11. b) M. J. Slater, S. Cockerill, R. Baxter, R. W. Bonser, K. Gohil, C. Gowrie, J. E. Robinson, N. Parry, R. Randall, W. Snowden, Bioorg. Med. Chem. 1999, 7, 1067.
12. a) M. Ohkubo, K. Kojiri, H. Kondo, S. Tanaka, H. Kawamot, T. Nishimura, I. Nishimura, T. Yoshinari, H. Arakawa, H. Suda, H. Morishima, S. Nishimura, Bioorg. Med. Chem. Lett. 1999, 9, 1219;
13. b) P. Moreau, M. Sancelme, C. Bailly, S. Leonce, A. Pierre, J. Hickman, B. Pfeiffer, M. Prudhomme, Eur. J. Med. Chem. 2001, 36, 887;
14. c) K. S. Lam, D. R. Schroeder, J. M. Veitch, K. L. Colson, J. A. Matson, J. W. C. Rose, T. W. Doyle, S. Forenza, J. Antibiot. 2001, 54, 1;
15. d) A. Voldoire, M. Sancelme, M. Prudhomme, P. Colson, C. Houssier, C. Bailly, S. Leonce, S. Lambel, Biorg. Med. Chem. 2001, 9, 357;
16. e) A. Marotto, Y. S. Kim, E. Schulze, U. Pindur, Pharmozie 2002, 57, 194.
17. B. A. Pfeifer, S. J. Admiraal, H. Gramajo, D. A. Cane, C. Khosla, Science 2001, 291, 1790.
18. T. Ohuchi, T. A. Ikeda-Araki, A. Watanabe-Sakamoto, K. Kojiri, M. Nagashima, M. Okanishi, H. Suda, J. Antibiot. 2000, 53, 393.
19. C.-G. Hyun, T. Bililign, J. S. Thorson, ACS Natl. Meet., Abstr. Pap. 2001, abstract Carb. 67.
20. C. Sanchez, I. A. Butovich, A. F. Brana, J. Rohr, C. Mendez, J. A. Salas, Chem. Biol. 2002, 9, 519.
21. a) P. R. August, T. H. Grossman, C. Minor, M. P. Draper, I. A. MacNeil, J. M. Pemberton, K. M. Call, D. Holt, M. S. Osburne, J. Mol. Microbiol. Biotechnol. 2000, 2, 513;
22. b) P. Ruhul, A. Z. M. Momen, T. Hoshino, Biosci. Biotechnol. Biochem. 2000, 64, 539.
23. C. Albermann, J. Liao, J. S. Thorson, unpublished results.
24. a) C. J. Pearce, T. W. Doyle, S. Forenza, K. S. Lam, D. R. Schroeder, J. Nat. Prod. 1988, 51, 937;
25. b) D. Meksuriyen, G. A. Cordell, J. Nat. Prod. 1988, 51, 893;
26. c) S. Lam, S. Forenza, T. W. Doyle, C. J. Pearce, J. Ind. Microbiol. 1990, 6, 291;
27. d) Yang, G. Cordell, J. Nat. Prod. 1997, 60, 788.
28. a) J. Jiang, J. B. Biggins, J. S. Thorson, J. Am. Chem. Soc. 2000, 122, 6803;
29. b) J. Jiang, J. B. Biggins, J. S. Thorson, Angew. Chem. 2001, 113, 1550-1553; Angew. Chem. Int. Ed. 2001, 40, 1502;
30. b) J. Jiang, J. B. Biggins, J. S. Thorson, Angew. Chem. 2001, 113, 1550-1553; Angew. Chem. Int. Ed. 2001, 40, 1502;
31. W. A. Barton, J. B. Biggins, J. Lesniak, P. D. Jeffrey, J. Jiang, K. R. Rajashankar, J. S. Thorson, D. B. Nikolov, Nat. Struct. Biol. 2001, 8, 545;
32. J. S. Thorson, T. J. Hosted, Jr., J. Jiang, J. B. Biggins, J. Ahlert, M. Ruppen, Curr. Org. Chem. 2001, 5, 139;
33. W. A. Barton, J. B. Biggins, J. Jiang, J. S. Thorson, D. B. Nikolov, Proc. Natl. Acad. Sci. USA 2002, 99, 13397-13402;
34. H. Losey, J. Jiang, J. B. Biggins, M. Oberthur, X.-Y. Ye, S. D. Dong, D. Kahne, J. S. Thorson, C. T. Walsh, Chem. Biol. 2002, in press.